JPH06343481A - Production of diglyceride - Google Patents
Production of diglycerideInfo
- Publication number
- JPH06343481A JPH06343481A JP5154516A JP15451693A JPH06343481A JP H06343481 A JPH06343481 A JP H06343481A JP 5154516 A JP5154516 A JP 5154516A JP 15451693 A JP15451693 A JP 15451693A JP H06343481 A JPH06343481 A JP H06343481A
- Authority
- JP
- Japan
- Prior art keywords
- diglyceride
- glycerin
- lipase
- fats
- oils
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 12
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims abstract description 46
- 235000011187 glycerol Nutrition 0.000 claims abstract description 23
- 239000003921 oil Substances 0.000 claims abstract description 23
- 102000004882 Lipase Human genes 0.000 claims abstract description 20
- 108090001060 Lipase Proteins 0.000 claims abstract description 20
- 239000004367 Lipase Substances 0.000 claims abstract description 20
- 235000019421 lipase Nutrition 0.000 claims abstract description 20
- 239000003925 fat Substances 0.000 claims abstract description 17
- 238000006243 chemical reaction Methods 0.000 claims abstract description 15
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 4
- 239000000194 fatty acid Substances 0.000 claims description 4
- 229930195729 fatty acid Natural products 0.000 claims description 4
- 150000004665 fatty acids Chemical class 0.000 claims description 4
- 235000021588 free fatty acids Nutrition 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 239000000470 constituent Substances 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims 1
- 150000004671 saturated fatty acids Chemical class 0.000 claims 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 claims 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 8
- 239000002253 acid Substances 0.000 abstract 1
- 235000019198 oils Nutrition 0.000 description 18
- 235000019197 fats Nutrition 0.000 description 13
- 239000000203 mixture Substances 0.000 description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- LDVVTQMJQSCDMK-UHFFFAOYSA-N 1,3-dihydroxypropan-2-yl formate Chemical compound OCC(CO)OC=O LDVVTQMJQSCDMK-UHFFFAOYSA-N 0.000 description 4
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 238000000199 molecular distillation Methods 0.000 description 3
- 235000014593 oils and fats Nutrition 0.000 description 3
- 235000019482 Palm oil Nutrition 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000009776 industrial production Methods 0.000 description 2
- 239000002540 palm oil Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 241000186063 Arthrobacter Species 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 241000588881 Chromobacterium Species 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 241000589540 Pseudomonas fluorescens Species 0.000 description 1
- 235000019484 Rapeseed oil Nutrition 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- OGBUMNBNEWYMNJ-UHFFFAOYSA-N batilol Chemical class CCCCCCCCCCCCCCCCCCOCC(O)CO OGBUMNBNEWYMNJ-UHFFFAOYSA-N 0.000 description 1
- 235000015278 beef Nutrition 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000003240 coconut oil Substances 0.000 description 1
- 235000019864 coconut oil Nutrition 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 235000012343 cottonseed oil Nutrition 0.000 description 1
- 239000002385 cottonseed oil Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 125000005456 glyceride group Chemical group 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 235000019871 vegetable fat Nutrition 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Abstract
Description
【０００１】[0001]
【産業上の利用分野】本発明は、リパーゼを用いてジグ
リセリドを製造する方法に関する。さらに詳しくは、油
脂とグリセリンとを特定のモル比、特定のリパーゼの存
在下に、特定の反応温度により、高濃度のジグリセリド
を製造する方法に関する。TECHNICAL FIELD The present invention relates to a method for producing diglyceride using lipase. More specifically, it relates to a method for producing a high-concentration diglyceride at a specific molar ratio of fats and oils and glycerin in the presence of a specific lipase at a specific reaction temperature.
【０００２】[0002]
【従来の技術及び発明が解決しようとする課題】ジグリ
セリドは、基材として、包装、食品、化粧品、医薬品な
どの分野で利用されている。ジグリセリドの製造は、通
常グリセリンと油脂とのグリセロリシス反応による方法
やグリセリンと脂肪酸とのエステル化反応による方法が
一般的である。工業的製法として最も代表的に行なわれ
ているのは、グリセロリシス反応である。例えば、グリ
セリンと油脂を触媒存在下に 230〜250 ℃、30〜60分で
反応を行っている。BACKGROUND OF THE INVENTION Diglyceride is used as a base material in the fields of packaging, food, cosmetics, pharmaceuticals and the like. The production of diglyceride is generally carried out by a method involving a glycerolysis reaction between glycerin and fats and oils or a method involving an esterification reaction between glycerin and fatty acids. The most typical industrial production method is the glycerolysis reaction. For example, glycerin and fats and oils are reacted in the presence of a catalyst at 230 to 250 ° C for 30 to 60 minutes.
【０００３】このようにして得られる反応生成物には、
ジグリセリドの他にモノグリセリド、トリグリセリド、
グリセリンが含まれている（例えばグリセリン／モノグ
リセリド／ジグリセリド／トリグリセリド＝12／52／31
／５（％））。The reaction product thus obtained includes
In addition to diglyceride, monoglyceride, triglyceride,
Contains glycerin (eg glycerin / monoglyceride / diglyceride / triglyceride = 12/52/31
/ 5 (%)).
【０００４】ジグリセリドを高濃度で得るためには、分
子蒸留などの処理が必要である。しかし、分子蒸留など
の処理によっても、ジグリセリドとトリグリセリドを生
産性よく分離することは、容易でない。また、これらの
工程は複雑な反応、蒸留工程、高真空維持、高温操作を
必要とするため製造コストが高くかつ高温による品質へ
の影響が避け難いという欠点がある。In order to obtain a high concentration of diglyceride, a treatment such as molecular distillation is necessary. However, it is not easy to separate diglyceride and triglyceride with good productivity even by treatment such as molecular distillation. In addition, these processes require complicated reactions, distillation processes, maintenance of high vacuum, and high-temperature operation, resulting in high manufacturing cost and unavoidable influence of high temperatures on quality.
【０００５】本発明の目的は、高温履歴を経ていない高
品質のジグリセリドを高濃度で複雑な工程を経ずに製造
する方法を提供しようとするものである。It is an object of the present invention to provide a method for producing a high-quality diglyceride which has not undergone a high temperature history at a high concentration without complicated steps.
【０００６】[0006]
【課題を解決するための手段】昨今では、低温でかつ簡
単に反応できるメリットからリパーゼ触媒の検討が盛ん
であり、特開昭62-19090号公報、特開昭64-71495号公報
なども例示することができるが、いずれも工業的観点か
らは、有機溶媒使用、複雑な工程など必ずしも満足でき
るものではない。このような状況下で本発明者らは、油
脂とグリセリンとを特定のモル比、特定のリパーゼの存
在下に特定の温度で反応させることにより、シグリセリ
ドを高濃度で得られることを見い出し、本発明を完成し
た。即ち、本発明は、炭素数Ｃ6 〜Ｃ22の脂肪酸を主構
成脂肪酸とする油脂とグリセリンとを特定のモル比、特
定のリパーゼの存在下に特定の温度で反応させることを
特徴とするジグリセリドの製造法に関するものである。
以下、本発明を詳述する。[Means for Solving the Problems] Recently, a lipase catalyst has been extensively studied because of its merit of easily reacting at low temperature, and examples thereof include JP-A-62-19090 and JP-A-64-71495. However, none of them is always satisfactory from the industrial viewpoint, such as using an organic solvent and complicated steps. Under such circumstances, the present inventors have found that a high molar concentration of glyceride can be obtained by reacting a fat and oil with glycerin at a specific molar ratio and in the presence of a specific lipase at a specific temperature. Completed the invention. That is, the present invention is characterized by reacting an oil or fat containing a fatty acid having 6 to 22 carbon atoms as a main constituent fatty acid with glycerin at a specific molar ratio in the presence of a specific lipase at a specific temperature. Of the manufacturing method of.
Hereinafter, the present invention will be described in detail.
【０００７】本発明で用いる油脂としては、一般的な動
植物油脂を挙げることができる。例えば菜種油、綿実
油、パーム油、大豆油、牛脂、ヤシ油、中鎖トリグリセ
リドなどを挙げることができる。さらに、これらの硬化
油脂、加工油脂、分別油脂も利用できる。The fats and oils used in the present invention include general animal and vegetable fats and oils. Examples thereof include rapeseed oil, cottonseed oil, palm oil, soybean oil, beef tallow, coconut oil, and medium-chain triglyceride. Further, these hardened oils and fats, processed oils and fats, and fractionated oils and fats can be used.
【０００８】本発明で用いるリパーゼは、シュードモナ
ス フルオレッセンス(Pseudomonusfluorescens）、ク
ロモバクテリウム ビスコーザム（Chromobacteriumvis
cosum）、アルスロバクター ウレアファシェンス（Art
hrobacterureafaciens)などを生産菌とするリパーゼを
使用することができる（特公平4-12710 号公報）。該リ
パーゼは、グリセリンと油脂の系の中で遊離のままで使
用できる。また、各種担体（セライト、ケイソウ土、シ
リカゲル、イオン交換樹脂など）に保持させた固定化リ
パーゼ製剤としても使用できる。The lipase used in the present invention includes Pseudomonus fluorescens and Chromobacterium viscosam.
cosum), Arthrobacter Urea Fascens (Art
It is possible to use a lipase whose production bacterium is hrobacter ureafaciens) (Japanese Patent Publication No. 4-12710). The lipase can be used as it is in the system of glycerin and oil. It can also be used as an immobilized lipase preparation which is held in various carriers (such as Celite, diatomaceous earth, silica gel, ion exchange resins).
【０００９】本発明において、油脂とグリセリンのモル
比は、油脂１モルに対し 0.2モル以上のグリセリンであ
る。好ましくは、油脂１モルに対し 0.5〜４モルで反応
を行なう。グリセリンの量がこの範囲より少なすぎると
グリセリンの量が不足して遊離脂肪酸が多くなり、製造
するジグリセリド含量が上昇しない。また逆に多すぎる
と無作用のグリセリンが増加し効率的でない。In the present invention, the molar ratio of oil / fat to glycerin is 0.2 mol or more of glycerin per 1 mol of oil / fat. Preferably, the reaction is carried out at 0.5 to 4 mol with respect to 1 mol of fats and oils. If the amount of glycerin is less than this range, the amount of glycerin will be insufficient and the amount of free fatty acids will increase, so that the diglyceride content produced will not increase. On the other hand, if the amount is too large, ineffective glycerin increases and it is not efficient.
【００１０】また本発明において、反応温度は多段階の
温度で規定される。ジグリセリドの収率や作業性などか
ら、３〜４段階の温度変化が好ましい。即ち、油脂とグ
リセリン及びリパーゼから成る混合物を多段階の温度で
変化させた時、ある温度では、遊離脂肪酸が生成しやす
くなったり、また、ある温度ではジグリセリドあるいは
モノグリセリド合成の方向へシフトしたりする。本発明
では、多段階の温度コントロールにより遊離脂肪酸、モ
ノグリセリド、トリグリセリドを極力生成させずに高濃
度のジグリセリドを得ることができた。Further, in the present invention, the reaction temperature is defined as a multi-step temperature. From the yield of diglyceride, workability, etc., a temperature change of 3 to 4 steps is preferable. That is, when a mixture of fats and oils, glycerin and lipase is changed at multi-step temperatures, free fatty acids are likely to be produced at a certain temperature, and diglyceride or monoglyceride synthesis is shifted at a certain temperature. . In the present invention, it was possible to obtain a high concentration of diglyceride without producing free fatty acids, monoglycerides and triglycerides by controlling the temperature in multiple stages.
【００１１】本発明のより具体的な方法は、以下に示す
通りである。即ち、油脂、グリセリン（水分２〜４重量
％）、リパーゼ（油脂１重量部に対し 1,000〜10,000 u
nits）から成る混合物を油脂の融点よりやや高い温度で
攪拌し、次に多段階で温度を変化させて、ジグリセリド
合成の方向に反応をシフトさせる。反応終了物より、リ
パーゼをろ別し、そのまま利用することもできる。さら
に未反応のグリセリン及びモノグリセリドを分子蒸留な
ど従来の分離、精製手段により容易に除去することもで
きる。また、分離したリパーゼは、繰り返し反応に用い
ることができる。A more specific method of the present invention is as follows. That is, oil and fat, glycerin (water content 2 to 4% by weight), lipase (1,000 to 10,000 u per 1 part by weight of oil and fat).
The mixture of nits) is stirred at a temperature slightly higher than the melting point of fats and oils, and then the temperature is changed in multiple stages to shift the reaction toward the diglyceride synthesis. It is also possible to filter the lipase from the reaction product and use it as it is. Further, unreacted glycerin and monoglyceride can be easily removed by conventional separation and purification means such as molecular distillation. The separated lipase can be used for repeated reactions.
【００１２】[0012]
【実施例】以下に、本発明の実施例と比較例をもって説
明するが本発明は、これらの実施例に限定されるもので
はない。[Examples] Examples of the present invention and comparative examples will be described below, but the present invention is not limited to these examples.
【００１３】（実施例１）グリセリン51ｇをステンレス
製タンクに入れ、シュードモナス フルオレッセンス産
生リパーゼ15ｇを加え、攪拌機で10分間攪拌してリパー
ゼとグリセリンを十分に混合した。次に予め溶解してお
いたパーム極度硬化油1508ｇをタンクに加え、65℃で
0.5時間攪拌した。次に温度を60℃に下げ２時間攪拌し
た。その後55℃で２時間、50℃で３日間反応を続け反応
終了物を得た。反応終了物の油分組成（％）を以下の分
析方法により求めた。Example 1 51 g of glycerin was placed in a stainless steel tank, 15 g of Pseudomonas fluorescens-producing lipase was added, and the mixture was stirred for 10 minutes with a stirrer to sufficiently mix the lipase and glycerin. Next, add 1508 g of pre-dissolved extremely hardened palm oil to the tank at 65 ° C.
It was stirred for 0.5 hours. Next, the temperature was lowered to 60 ° C. and the mixture was stirred for 2 hours. Then, the reaction was continued at 55 ° C. for 2 hours and at 50 ° C. for 3 days to obtain a reaction-terminated product. The oil composition (%) of the reaction finished product was determined by the following analytical method.
【００１４】（分析方法）反応終了油約 200mgにクロロ
ホルム 3.0mlを加えて浸とうし、１時間以上放置して反
応を停止させた。その後、水で数回洗浄することによっ
て、グリセリン、リパーゼを除去し、油分を含むクロロ
ホルム溶液を得た。クロロホルムを留去後、油分組成
（％）を高速液体クロマトグラフィーにより求めた。(Analytical Method) About 200 mg of the reaction-completed oil was added with 3.0 ml of chloroform, and the mixture was stirred and allowed to stand for 1 hour or more to stop the reaction. Then, by washing with water several times, glycerin and lipase were removed, and a chloroform solution containing oil was obtained. After the chloroform was distilled off, the oil composition (%) was determined by high performance liquid chromatography.
【００１５】実施例１の反応方法及び分析結果を表１に
示した。以下、実施例２〜実施例６、及び比較例１〜比
較例４も実施例１と同様の操作を行なった。これらの結
果を表１及び表２に示した。Table 1 shows the reaction method and analysis results of Example 1. Hereinafter, the same operations as in Example 1 were performed in Examples 2 to 6 and Comparative Examples 1 to 4. The results are shown in Tables 1 and 2.
【００１６】[0016]
【表１】 [Table 1]
【００１７】[0017]
【表２】 [Table 2]
【００１８】[0018]
【発明の効果】本発明は、高温履歴を経ていない高品質
のジグリセリドを高濃度で複雑な工程を経ずに製造する
ことができ、工業的製法として提供することができる。INDUSTRIAL APPLICABILITY The present invention can produce a high-quality diglyceride that has not undergone high-temperature history at a high concentration without complicated steps, and can be provided as an industrial production method.
Claims (3)
脂肪酸を主構成脂肪酸とする油脂とグリセリンとを特定
のモル比、特定のリパーゼの存在下に特定の温度で反応
させることを特徴とするジグリセリドの製造法。1. An oil and fat containing a saturated or unsaturated fatty acid having 6 to 22 carbon atoms as a main constituent fatty acid and glycerin are reacted at a specific molar ratio in the presence of a specific lipase at a specific temperature. And a method for producing diglyceride.
ルに対し 0.2モル以上のグリセリンであり、リパーゼが
グリセロリシス反応を進行し、かつ遊離脂肪酸が生成し
にくいリパーゼである請求項１記載のジグリセリドの製
造法。2. The diglyceride according to claim 1, wherein the molar ratio of fats and oils to glycerin is 0.2 mol or more per 1 mol of fats and oils, and the lipase is a lipase which undergoes a glycerolysis reaction and is unlikely to produce free fatty acids. Manufacturing method.
求項１又は２記載のジグリセリドの製造法。3. The method for producing a diglyceride according to claim 1 or 2, wherein the reaction temperature is defined in multiple stages.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5154516A JPH06343481A (en) | 1993-06-02 | 1993-06-02 | Production of diglyceride |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5154516A JPH06343481A (en) | 1993-06-02 | 1993-06-02 | Production of diglyceride |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH06343481A true JPH06343481A (en) | 1994-12-20 |
Family
ID=15585962
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP5154516A Pending JPH06343481A (en) | 1993-06-02 | 1993-06-02 | Production of diglyceride |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH06343481A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2000003031A1 (en) * | 1998-07-09 | 2000-01-20 | Kao Corporation | Process for producing partial glyceride |
-
1993
- 1993-06-02 JP JP5154516A patent/JPH06343481A/en active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2000003031A1 (en) * | 1998-07-09 | 2000-01-20 | Kao Corporation | Process for producing partial glyceride |
| US6337414B1 (en) * | 1998-07-09 | 2002-01-08 | Kao Corporation | Process for producing partial glyceride |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Linfield et al. | Enzymatic fat hydrolysis and synthesis | |
| EP1717318B1 (en) | Process for producing fat or oil | |
| JP3720194B2 (en) | Method for producing partial glycerides | |
| CA2299704C (en) | Process for producing diglycerides | |
| AU2005200356A1 (en) | Methods for producing alkyl esters | |
| JPH0439995B2 (en) | ||
| JPH0338837B2 (en) | ||
| JPH0542260B2 (en) | ||
| JPH0716425B2 (en) | Transesterification method for fats and oils | |
| JPH08294394A (en) | Production of diglyceride | |
| JPH0416519B2 (en) | ||
| AU628644B2 (en) | Enzymatic transesterification of tryglycerides | |
| JP3847445B2 (en) | Diglyceride production method | |
| JPH06343481A (en) | Production of diglyceride | |
| JP2002088392A (en) | Method for ester interchange of oils or fats | |
| JP4945838B2 (en) | Oil and fat manufacturing method | |
| JP4168933B2 (en) | Process for producing processed glycerides | |
| JPH0665310B2 (en) | Method for producing diglyceride | |
| JP3880095B2 (en) | Method for purifying highly unsaturated fatty acids | |
| US6825368B2 (en) | Method for producing a fatty acid | |
| JP3773315B2 (en) | Method for purifying omega-3 highly unsaturated fatty acid ester | |
| JP6194908B2 (en) | Oil and fat manufacturing method | |
| JPS60251891A (en) | Method of ester interchange reaction of fat and oil | |
| JPS62201591A (en) | Glycerolysis of oil and fat | |
| JPH01108990A (en) | Production of oil and fat |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A02 | Decision of refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A02 Effective date: 20040114 |